Light-harvesting macroring accommodating a tetrapodal ligand based on complementary and cooperative coordinations

Journal of the American Chemical Society
Yusuke KuramochiYoshiaki Kobuke

Abstract

A porphyrin macroring, mimicking the light-harvesting complex of photosynthetic purple bacteria, was synthesized by self-assembling trisporphyrinatoZn(II) complexes with imidazolyl substituents at both molecular terminals. Very strong complementary coordination of imidazolyl to Zn(II) afforded exclusively the cyclic trimer of trisporphyrin under dilute conditions at 27 degrees C in CHCl3/MeOH = 9/1 (v/v). 1H NMR spectra of the macroring indicate the existence of two topological isomers, one symmetric and one asymmetric. Use of three noncoordinated porphyrinatoZn(II) sites allows a tetrapodal ligand to be incorporated into the cavity of the macroring. A Job plot and the clear bending behavior on UV-vis titration indicated the formation a 1:1 complex; the heterogeneity of two topological isomers was not observed, and both isomers similarly accommodated the tetrapodal ligand. The association constant obtained by curve fitting analysis was 8 x 108 M-1 in toluene. This large association constant reflects the cooperative nature of three coordination sites.

References

Feb 27, 2003·Journal of the American Chemical Society·Ryoichi Takahashi, Yoshiaki Kobuke

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Citations

Apr 1, 2006·Chemical Communications : Chem Comm·Hiromichi NakagawaYoshiaki Kobuke
May 31, 2007·Chemical Society Reviews·Yasuyuki NakamuraAtsuhiro Osuka
Jul 18, 2008·Chemical Communications : Chem Comm·Joanne DyYoshiaki Kobuke
Sep 2, 2008·Chemical Communications : Chem Comm·Naoki Aratani, Atsuhiro Osuka
Mar 8, 2011·Chemical Communications : Chem Comm·James W LeelandJason B Love
Jun 29, 2018·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Yusuke KuramochiAkiharu Satake
Feb 21, 2009·Chemistry : a European Journal·Andreas LohrFrank Würthner
Jul 6, 2007·Chemistry : a European Journal·Marga C LensenRoeland J M Nolte
Jan 30, 2008·Chemistry : a European Journal·Yusuke KuramochiYoshiaki Kobuke
May 29, 2008·Angewandte Chemie·Markus HoffmannHarry L Anderson
Feb 23, 2010·Chemistry : a European Journal·Jianxin SongAtsuhiro Osuka
Oct 27, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Aline M J Devoille, Jason B Love
Jun 12, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Keiko YoneyamaAkiharu Satake
Feb 24, 2007·Angewandte Chemie·Markus HoffmannHarry L Anderson
Aug 30, 2008·Angewandte Chemie·Bart M J M Suijkerbuijk, Robertus J M Klein Gebbink
Sep 5, 2015·Chemistry : a European Journal·Weiming HuangJianxin Song
Nov 28, 2008·Chemistry : a European Journal·Kent A NielsenJan O Jeppesen
Jan 13, 2011·Chemistry : a European Journal·Akiharu SatakeYoshiaki Kobuke
Mar 24, 2009·Chemical Reviews·Irina BeletskayaChristine Stern
Apr 29, 2008·Journal of the American Chemical Society·Akiharu SatakeYoshiaki Kobuke
Feb 12, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Ryo Sasaki, Shigeru Murata
Dec 18, 2008·Journal of the American Chemical Society·Naoto NagataYoshiaki Kobuke
Nov 6, 2009·The Journal of Organic Chemistry·Tommaso CarofiglioAlessandro Varotto
Mar 25, 2005·The Journal of Organic Chemistry·Ryoichi Takahashi, Yoshiaki Kobuke
Jun 26, 2021·Chemical Science·Tom KeijerJoost N H Reek
Aug 24, 2013·Journal of the American Chemical Society·Tatsuki MorimotoOsamu Ishitani
Nov 30, 2018·Inorganic Chemistry·Yasuomi YamazakiOsamu Ishitani
Nov 21, 2012·Organic Letters·Karl J Thorley, Frank Würthner
Sep 10, 2019·Inorganic Chemistry·Yasuomi Yamazaki, Osamu Ishitani
Dec 31, 2019·Journal of the American Chemical Society·Yusuke KuramochiAkiharu Satake
Jul 15, 2006·The Journal of Organic Chemistry·Tsutomu Ishi-iShuntaro Mataka

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